The 7 Richest Pirates in History

The life of a pirate has a romanticized aura – most stories paint a picture of swashbuckling men who sailed through the high seas unafraid to take what they wanted, the endings were never quite as happy though. Would it surprise you to learn that a lot of pirates actually had the blessing of their government?

Beginning in the 1500s, enterprising sailors realized that there was another method of earning money other than carrying passengers or cargo over the high seas. Many men who began their trade on the sea in a legitimate way soon realized that they could make a ton of money by hiring themselves out as privateers.

bissig /

bissig /

Privateers were sailors who were given letters of permission (called letters of marque) from their governments to attack foreign vessels in order to secure more ships, men, and money for their national fleet. Technically, these people weren’t considered pirates – privateers were a legal and useful tool during war time. Because of their similar qualifications, there are many privateers on the list of the richest pirates in history, as they brought in tons of gold and bounty – both for their country and for themselves.

Samuel “Black Sam” Bellamy

Not a lot is known about Samuel Bellamy’s life. His early travels took him to Massachusetts, where he met the young Maria Hallett. Although he had a wife and child at home in England, he fell madly in love with Maria. He left Massachusetts, vowing to come back and marry her when he had earned enough money to support her.

After many months with the Navy, Bellamy felt restless and unsatisfied, so he joined a pirate ship captained by Benjamin Hornigold. Within a few months, Hornigold’s crew revolted and installed Bellamy as their new captain. In one year, they robbed 50 ships, and only a year later, they hit the jackpot. They boarded a ship called Whydah, which was packed full of valuable cargo – enough for the entire crew to retire on. Forbes estimates that Bellamy’s share of this haul would equal roughly $120 million dollars today.


Sir Francis Drake

Although to the English, Sir Francis Drake has always been a national hero (known for carrying out the second circumnavigation of the globe), for the Spaniards, Drake will always be first and foremost a pirate. Even though he has many honors that were granted to him in his work as a soldier, politician, and explorer, his primary income came from raids on the Spanish armada.

In his early twenties, he conducted many raids on Spanish-owned territory in what is now Panama. However, it wasn’t until a few years later that he began pulling in truly valuable ships. In 1578, Drake captured a Spanish ship that was laden down with gold, jewels, and silver amounting to $7 million in today’s dollars. Overall, modern estimates of his lifetime haul of treasure put it at roughly $115 million.

ian woolcock /

ian woolcock /

Thomas Tew

Even though Thomas Tew only undertook two major expeditions onboard a pirate ship in his lifetime, he managed to bring in tons of valuable commodities. He also pioneered the route that many pirates following in his footsteps dubbed the “Pirate Round”.

Tew came into being a pirate fairly late in life. He was born in 1649, but he didn’t get a letter of marque until 1692. He set sail as a legitimate privateer, but he revealed to his crew that he not only planned to attack his targets, but also wished to pirate other vessels along the way. His overall lifetime earnings ring in at around $103 million dollars in modern currency.

iurii /

iurii /

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